


Round Two Please!

by angelsandidjits



Series: What Dean Does When He's Bored [2]
Category: Supernatural
Genre: Cumslut!Dean, Double Penetration, Gangbang, Handcuffs, Multi, Office Sex, Rough Sex, Spitroasting, bottom!Dean, cockslut!Dean
Language: English
Status: Completed
Published: 2015-05-31
Updated: 2015-05-31
Packaged: 2018-04-02 04:27:17
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 2,047
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/4045921
Author URL: https://archiveofourown.org/users/angelsandidjits/pseuds/angelsandidjits
Summary: <blockquote class="userstuff">
      <p>You guys asked for it so here it is! Dean goes back for a second round. This is a sequel, but can also be read as a standalone.</p>
    </blockquote>





	Round Two Please!

**Author's Note:**

> You guys asked for it so here it is! Dean goes back for a second round. This is a sequel, but can also be read as a standalone.

It’d been 6 months since that last good fuck, and Dean still has that card. He’d been holding on to it in the hope of going back, but he hasn’t had the time, with all the weird shit going on. But it’s been 6 freaking months and he can’t wait any longer. Besides, they were in a motel not too far from the address listed on the back of the card. So Dean, impatient as ever, decided he was gonna go get some. Little did he know what he was getting into.

He arrives at the address, which turns out to look like an abandoned warehouse, complete with a dried up well on the side and a small garage. Looking through the small windows situated on the sides of the garage, he sees a number of low riding bikes parked, and he instantly knows he’s in the right place. The ‘barren warehouse’ look is merely a ruse, there’s probably a drug factory underneath that looks straight out of the set of Breaking Bad. You know based on that stereo type that bikies = drugs. 

There seems to be no way- that he can physically see- to get into this odd building, so he has no other choice, than to make himself known. Guns blazing and all.  
So that’s what he does, or at least he tries to do. He doesn’t make it 5 steps past the shards of the broken window glass and rows of bikes, before he’s surrounded by 3 burly men wearing those same emblazoned jackets he saw at the bar those few months back. These men were either not present that night, or have forgotten who he was, because they disarm him and handcuff him (which is doesn’t normally happen at a drug factory, right?). Unlikely that it was the latter, he knew he was an unforgettable fuck. The 3 men escort him further into the warehouse, in through some corridors, a lift which takes them to a lower floor; which is much better furnished than the upper level. 

They open the door and push him into the room. “Look what we found snooping around and making a mess, boss,” says one of them in a squeaky voice reminiscent of a cartoon character.  
“This guy just busts in through one of the garage windows, not a care in the world”.  
Dean recognizes the boss whose sitting behind the desk as the older man who handed him the card that got him here in the first place.  
“Boss, what do you want us to do with him?” asks the squeaky- voiced man. “Boy like this would make a good addition to the headless scarecrows we’ve got in the farm”

“No, you are to do nothing of the sort to him” the boss replies before adding “He’s here for a far greater purpose” He looks at the cartoon-voiced man and tells him to fetch his secretary for him and signals to the other two to leave.

The grey-haired man gets up from behind his desk and walks past Dean to stand behind his back “I was wondering when you’d show up.” He takes a bunch of keys from his pocket and unlocks the handcuffs on Dean’s wrists.  
“Well…” Dean tries to say before the older man continues  
“Although you did surprise me, by holding back for so long. And I don’t like waiting, but I’ll forgive you based on the fact that you have to be one of the best cocksluts I’ve ever seen” He walks to the front and faces Dean, then extends his hand “Since you’re gonna be here for a while, you should probably know my name, Reggie, since that should be the only name coming out of your slutty mouth in a few minutes.”  
“The name’s Spencer and I cant wait” Dean replies with a smirk.

Dean expected the summoned secretary to be a blonde with big tits half popping out of a tiny top, but instead it was a smoking hot guy with dark brown hair and piercing blue eyes, in a striking suit that accentuated his lankiness and svelte form that walked in.

“You called for me boss?” the secretary says matter-of-factly.  
“Yes I did, Larry. Do I have any appointments left for today?”  
“One at 12, sir”  
“Cancel it. After that I want you to call Anther, Giddy, Ben, Sleepy and Greydan in here and tell them I’ve got them a surprise for them.” He pauses. “Oh and tell them to bring their hardest worker with them as well”  
“Yes sir.” The man turned around to leave and Dean found himself hardening at the sight of those perky butt-cheeks walking away from the room, as well as the anticipation of getting thoroughly fucked by what he hoped (by his calculations) was at least 10 men.

A few minutes pass, Dean takes the time to walk around the room and observe the grandeur of it before stopping in front a great big painting of what seems to be a younger version of Reggie. Reggie asks him if he’d like a drink or something, which he politely refuses. He then asks Dean to strip, which he does eagerly. 

“Just as gorgeous as the day I left it” Reggie says in reference to Dean’s ass which is followed by a hard smack. “Have you prepared yourself?”  
“A little yea”  
“Let’s see how much” He says as he pushes Dean’s head into the sofa in front of him and inserts two fingers into Dean’s ass. “Oh wow that’s a more than just a little prepared” he remarks as he adds a third finger into Dean’s lubricated asshole. “How bad do you want to be fucked huh, Spencer?”  
“There’s nothing I want more right now” Dean remarks.  
“Good answer” Reggie replies. And just as he says that all the people (Dean assumes) that Reggie called on, enter one by one into the office. Reggie also calls on Larry to stay and Dean finds himself more excited than ever.

“Now gents, what I have here is a special treat, considering all the hard work you all have been putting into our quickly expanding business these few months. This here is Spencer” he pauses to gesture at Dean and then continues, “a pretty cockslut we found back in New Farm and he’s ready for a good pounding. He’s really eager, I don’t know if you can tell by that hard cock, but go ahead and help yourself lads, you deserve it.” 

A few of the men seem to be in disbelief at the sight of his pretty ass that’s on display, while others waste no time in unbuckling their belts and taking out their cocks, and trying to feel him up. Two men walk up to either side of Dean, one shifts him, so that he can sit down and his cock goes into Dean’s mouth, while the other man penetrates him slowly but steadily. Dean can’t help but moan as the man behind him slowly picks up pace and starts earnestly fucking him. “Such a tight hole” the man says. To which the man fucking Dean’s face says, “Wait till you get a feel of his mouth Greydan, probably wouldn’t last 30 seconds on this side”  
Another two men sit down on the sofa, beside the man whose cocks’ in his mouth. They each pick up his hands and place it on their cocks. He’s amazed that he can actually balance, but before he has any time to think, the man directly in from of him holds onto the short strands of hair on the back of his head and fucks his throat. He makes a loud noise and soon cums in Dean’s mouth, and all the men cheer him on. He shakes the left over cum onto Dean’s face and moves aside, so that someone else could start fucking his mouth. The two men who were on either side lift him up so that he can suck them both at the same time. Mean while Greydan, behind him starts to falter in his movements and Dean knows that load number two is on the way. 

After he’s had three loads in his ass, they decide, its time he takes two cocks in his ass. One man, called Sleepy, Dean remembers, lifts Dean off the ground and puts him up onto his hips, forcing Dean to wrap his legs around him. While Sleepy guides his cock into his sloppy hole, another man stands behind Dean and places his cock alongside Sleepy’s and Dean has never felt so full in his life. They don’t wait too long before they start lifting and pulling Dean hard onto their cocks and Dean cant help but scream at the fullness, and the feeling of them nailing his prostate with every snap of their hips. ‘Harder, oh yea, right there, faster, please’ Dean begs. Two minutes later, Dean cums untouched and his fluttering hole causes both men to cum inside him at the same time.

Reggie handcuffs Dean with his hands behind his back and guides him to his desk. He pushes Dean onto the desk and spreads his legs apart so his ass is exposed and the two loads of cum runs down his beautiful, freckled legs. Reggie sits himself down on his desk chair and lifts his chair so that it’s inline with Dean’s mouth. No one dares move forward while the boss fucks him. But then Reggie calls over Larry and says “Larry I want you to fuck his ass so hard he either sees stars or faints. We’ve all heard the stories about your cock, so show us how good it is now.” Larry doesn’t need to be told twice, and Dean can see what Reggie means, because the second Larry’s cock is in his ass, he hits his A-spot and he starts seeing little glowy dots and he cant help but make loud noises that the whole building could probably hear.

The desk fuck makes Dean lose track of time, but he does notice that Reggie doesn’t cum, but brings himself really close, before stopping. ‘I want your cum Reggie, please’ Dean says and although unintentional Dean hears himself whimpering at the loss. ‘Don’t worry darling I’ll be back to wreck your tight little hole’ Reggie replies. Dean doesn’t even see where Reggie goes as there another cock is placed in Dean’s mouth. This guy cums so quick, Dean didn’t even count to 10. Larry eventually cums in his ass, which also sets Dean off, who almost blacks out from the sheer pleasure.

After Larry leaves Dean is pulled back to the sofa, and his hands are uncuffed, brought to the front and handcuffed again. He is made to lie on his back and then a cock is placed in his ass, one in his hands and another down his throat. These men clearly enjoyed his previous performances, as it didn’t take them too long to blow their load in their respective fucking places. By now, Dean is sure that every man in the room has fucked him at least once.

Round two, consists of him being placed on the desk while all the men stand around him and take turns coming in his mouth. By the end Dean is so full of cum, he honestly feels like he’s had 3 burgers with the lot, along with the pie on the side.

“Did you enjoy the slut lads?” Reggie asks in a tone contrary to the blissed out mood of the room. A murmur of ‘mmhmm’s and ‘fuck yea’s are generally echoed around the room. “What do you think, should we keep him for a couple more days?”

“Yea, maybe the workers down at the factory could benefit from some de-stressing as well!” says someone in the back of the room.  
“That’s a good idea, I’m glad you’re happy to share, its what we’re all about, after all” says Reggie. Despite enjoying himself thoroughly, Dean finds his body giving into the tiredness and soreness that comes with a good, rough fuck session. He doesn’t hear the men dressing up and filing out of the room, the same way they came in. And he barely registers Larry lifting him up and placing him in his own bed.


End file.
